journal article·2018-10

Facile, productive, and cost-effective synthesis of a novel tetrazine-based iron oxide nanoparticle for targeted image contrast agents and nanomedicines

Marco M. Meloni, Stephen Barton, Alexandru Chivu, Juan C. Kaski, Wenhui Song, Taigang He

Journal of Nanoparticle Research· Volume 20· Issue 10
Publisher page

Abstract

We have developed an operationally simple, time, and cost-effective protocol to produce a novel tetrazine-based iron oxide nanoparticle using commercially available and inexpensive materials. Our protocol proceeds at room temperature and uses hexafluorophosphate azabenzotriazole tetramethyl uronium, a well-known, widely used reagent for the large-scale industrial production of important pharmaceuticals. The nanoparticles obtained have a diameter range between 16 and 21 nm and showed no toxicity against endothelial cell lines. The tetrazine moiety on the nanoparticle surface could potentially allow further attachment of specific targeting vectors by using so-called copper-free click chemistry. We therefore anticipate that our protocol can represent a significant breakthrough in the future development and commercialization of improved, tissue-specific contrast agents and drug delivery for clinical diagnosis, monitoring and therapy of diseases at an asymptomatic stage.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Click Chemistry and Applications · Advanced biosensing and bioanalysis techniques · Monoclonal and Polyclonal Antibodies Research

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (19)

Show source-provided references
1. Baskin JM, Prescher JA, Laughlin ST, Agard NJ, Chang PV, Miller IA, Lo A, Codelli JA, Bertozzi CR (2007) Copper-free click chemistry for dynamic in vivo imaging. Proc Natl Acad Sci U S A 104:16793–16797. https://doi.org/10.1073/pnas.070709010410.1073/pnas.0707090104 ↗
2. Colombo M, Carregal-Romero S, Casula MF, Gutierrez L, Morales MP, Bohm IB, Heverhagen JT, Prosperi D, Parak WJ (2012) Biological applications of magnetic nanoparticles. Chem Soc Rev 41:4306–4334. https://doi.org/10.1039/c2cs15337h10.1039/c2cs15337h ↗
3. Debets MF, van Berkel SS, Schoffelen S, Rutjes FP, van Hest JC, van Delft FL (2010) Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition. Chem Commun 46:97–99. https://doi.org/10.1039/b917797c10.1039/b917797c ↗
4. Devaraj NK, Weissleder R (2011) Biomedical applications of tetrazine cycloadditions. Acc Chem Res 44:816–827. https://doi.org/10.1021/ar200037t10.1021/ar200037t ↗
5. Dunetz JR, Magano J, Weisenburger GA (2016) Large-scale applications of amide coupling reagents for the synthesis of pharmaceuticals. Org Process Res Dev 20:140–177. https://doi.org/10.1021/op500305s10.1021/op500305s ↗
6. Evans HL, Nguyen QD, Carroll LS, Kaliszczak M, Twyman FJ, Spivey AC, Aboagye EO (2014) A bioorthogonal (68) Ga-labelling strategy for rapid in vivo imaging. ChemComm 50:9557–9560. https://doi.org/10.1039/c4cc03903c10.1039/c4cc03903c ↗
7. Haun JB, Devaraj NK, Hilderbrand SA, Lee H, Weissleder R (2010) Bioorthogonal chemistry amplifies nanoparticle binding and enhances the sensitivity of cell detection. Nat Nanotechnol 5:660–665. https://doi.org/10.1038/nnano.2010.14810.1038/nnano.2010.148 ↗
8. Herranz F, Morales MP, Roca AG, Vilar R, Ruiz-Cabello J (2008) A new method for the aqueous functionalization of superparamagnetic Fe2O3 nanoparticles. Contrast Media Mol Imaging 3:215–222. https://doi.org/10.1002/cmmi.25410.1002/cmmi.254 ↗
9. Jaradat DMM (2018) Thirteen decades of peptide synthesis: key developments in solid phase peptide synthesis and amide bond formation utilized in peptide ligation. Amino Acids 50:39–68. https://doi.org/10.1007/s00726-017-2516-010.1007/s00726-017-2516-0 ↗
10. Kolhatkar AG, Nekrashevich I, Litvinov D, Willson RC, Lee TR (2013) Cubic silica-coated and amine-functionalized FeCo nanoparticles with high saturation magnetization. Chem Mater 25:1092–1097. https://doi.org/10.1021/cm304111z10.1021/cm304111z ↗
11. Kuzmin A, Poloukhtine A, Wolfert MA, Popik VV (2010) Surface functionalization using catalyst-free azide−alkyne cycloaddition. Bioconjug Chem 21:2076–2085. https://doi.org/10.1021/bc100306u10.1021/bc100306u ↗
12. McKay CS, Finn MG (2014) Click chemistry in complex mixtures: bioorthogonal bioconjugation. Chem Biol 21:1075–1101. https://doi.org/10.1016/j.chembiol.2014.09.00210.1016/j.chembiol.2014.09.002 ↗
13. Meloni MM, Barton S, Xu L, Kaski JC, Song W, He T (2017) Contrast agents for cardiovascular magnetic resonance imaging: an overview. J Mater Chem B 5:5714–5725. https://doi.org/10.1039/c7tb01241a10.1039/c7tb01241a ↗
14. Mishra SK, Kumar BS, Khushu S, Tripathi RP, Gangenahalli G (2016) Increased transverse relaxivity in ultrasmall superparamagnetic iron oxide nanoparticles used as MRI contrast agent for biomedical imaging. Contrast Media Mol Imaging 11(5):350–361. https://doi.org/10.1002/cmmi.169810.1002/cmmi.1698 ↗
15. Morawski AM, Lanza GA, Wickline SA (2005) Targeted contrast agents for magnetic resonance imaging and ultrasound. Curr Opin Biotechnol 16:89–92. https://doi.org/10.1016/j.copbio.2004.11.00110.1016/j.copbio.2004.11.001 ↗
16. Ohgushi M, Nagayama K, Wada A (1978) Dextran-magnetite: a new relaxation reagent and its application to T2 measurements in gel systems. J Magn Reson 29:599–601. https://doi.org/10.1016/0022-2364(78)90018-510.1016/0022-2364(78)90018-5 ↗
17. Oliveira BL, Guo Z, Bernardes GJL (2017) Inverse electron demand Diels-Alder reactions in chemical biology. Chem Soc Rev 46:4895–4950. https://doi.org/10.1039/c7cs00184c10.1039/c7cs00184c ↗
18. Schmitz SA, Taupitz M, Wagner S, Wolf K-J, Beyersdorff D, Hamm B (2001) Magnetic resonance imaging of atherosclerotic plaques using superparamagnetic iron oxide particles. J Magn Reson Imaging 14:355–361. https://doi.org/10.1002/jmri.119410.1002/jmri.1194 ↗
19. Trivedi RA, U-King-Im JM, Graves MJ, Kirkpatrick PJ, Gillard JH (2004) Noninvasive imaging of carotid plaque inflammation. Neurology 63:187–188. https://doi.org/10.1212/01.wnl.0000132962.12841.1d10.1212/01.wnl.0000132962.12841.1d ↗